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Design, synthesis, and biological evaluation of analogues of the antitumor agent, 2-{4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy}propionic acid (XK469)

2-{4-[(7-Chloro-2-quinoxalinyl)oxy]phenoxy}propionic acid (XK469) is among the most highly and broadly active antitumor agents to have been evaluated in our laboratories and is currently scheduled to enter clinical trials in 2001. The mechanism or mechanisms of action of XK469 remain to be elaborated. Accordingly, an effort was initiated to establish a pharmacophore hypothesis to delineate the requirements of the active site, via a comprehensive program of synthesis of analogues of XK469 and evaluation of the effects of structural modification(s) on solid tumor activity. The strategy formulated chose to dissect the two-dimensional parent structure into three regions – I, ring A of quinoxaline; II, the hydroquinone connector linkage; and III, the lactic acid moiety – to determine the resultant in vitro and in vivo effects of chemical alterations in each region. Neither the A-ring unsubstituted nor the B-ring 3-chloro-regioisomer of XK469 showed antitumor activity. The modulating antitumor effect(s) of substituents of differing electronegativities, located at the several sites comprising the A-ring of region I, were next ascertained. Thus, a halogen substituent, located at the 7-position of a 2-{4-[(2-quinoxalinyl)oxy]phenoxy}propionic acid, generated the most highly and broadly active antitumor agents. A methyl, methoxy, or an azido substituent at this site generated a much less active structure, whereas 5-, 6-, 8-chloro-, 6-, 7-nitro, and 7-amino derivatives all proved to be essentially inactive. When the connector linkage (region II) of 1 was changed from that of a hydroquinone to either a resorcinol or a catechol derivative, all antitumor activity was lost. Of the carboxylic acid derivatives of XK469 (region III), i.e., CONH2, CONHCH3, CON(CH3)2, CONHOH, CONHNH2, CN, or CN4H (tetrazole), only the monomethyl- and N,N-dimethylamides proved to be active.

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Quinoxaline – Wikipedia,
Quinoxaline | C8H6N1058 | ChemSpider

Brief introduction of 2,3-Dichloroquinoxaline

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2213-63-0, Name is 2,3-Dichloroquinoxaline, belongs to quinoxaline compound, is a common compound. 2213-63-0In an article, authors is Ashry, E.S.H. El, once mentioned the new application about 2213-63-0.

Microwave Irradiation for Accelerating Organic Reactions – Part II: Six-, Seven-Membered, Spiro, and Fused Heterocycles

The use of microwave irradiation (MWI) as a nonconventional source of energy, a consequence of converting electromagnetic energy, had become very attractive for its applications to chemistry and material processing. In organic synthesis, the potential of microwave (MW) as a tool for heating attracted much interest soon after the work of Gedye (86TL279) and Giguere (86TL4945) in 1986. The terminology for the introduction of MW for organic reaction enhancement (MORE) and/or MW-assisted organic synthesis (MAOS) enabled access or parallel synthesis of various classes of compounds in organic chemistry. Although in the beginning some obstacles were faced by chemists using this technology, their desire led to the development of methods for the concurrent use of MW. One of these achievements involves the performance of organic reactions under solvent-free conditions: dry media in open vessels. Moreover, equipment and reactors have been developed and have become commercially available. Nowadays, MW activations are widely used in organic chemistry as shown by the increased number of publications. Available reviews include (91OPP683, 95AJC1665, 95T10403, 97CSR233, 97MI1, 98CSR213, 98CJC525, 98S1213, 99AJC83, 99JHC1565, 99MI1, 99MI2, 99MI3, 99T10851, 00CSR239, 00MI1, 01MI1, 01MI2, 01T4365, 01T9199, 01T9225, 02ACR717, 02MI1, 02MI2, 02MI3, 02T1235, 03MI1, 03MI2, 04H903, 05AHC1). The rapid expansion and popularity of assisting a wide range of organic reactions by exposure to MW have been accompanied by achieving reactions under solvent-free conditions, reducing reaction times, and increasing the yield of products and even selectivity. Moreover, in addition to the economic impact, there are additional advantages such as the use of noncorrosive, inexpensive, and environment-friendly catalysts, thus leading to eco-friendly approaches known as “green chemistry”. All these have attracted our attention to review the available literature on the role of MW in the field of heterocyclic chemistry, but owing to the increased number of publications led us first to publish “Microwave Irradiation for Accelerating Organic Reactions. Part I: Three, Four and Five Membered Heterocycles” in a former volume (05AHC1). This new chapter will be the second part including six-, seven-membered, spiro, and fused heterocyclic ring systems. Our survey of the literature on the synthesis and reactions of these heterocycles has been divided according to the number of heteroatoms in the heterocycles. The fused heterocycles are located according to the heterocycle that was built under MWI or as a reaction of these heterocycles acting as precursors. Each type is reviewed by first presenting their methods of preparation of the desired ring followed by its reactions. Heterocycles having either fused benzene or other heterocyclic rings have been located under a separate title when enough literature has been reported.

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Simple exploration of 2-Chloroquinoxaline

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Photoredox-Catalysed Decarboxylative Alkylation of N-Heteroarenes with N-(Acyloxy)phthalimides

An iridium photoredox catalyst in combination with either a stoichiometric amount of Br¡ãnsted acid or a catalytic amount of Lewis acid is capable of catalyzing regioselective alkylation of N-heteroarenes with N-(acyloxy)phthalimides at room temperature under irradiation. A broad range of N-heteroarenes can be alkylated using a variety of secondary, tertiary, and quaternary carboxylates. Mechanistic studies suggest that an IrII/IrIIIredox catalytic cycle is responsible for the observed reactivity.

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Green oxidant H2O2 as a hydrogen atom transfer reagent for visible light-mediated Minisci reaction

A visible light-mediated “green” protocol for metal-free oxidative coupling of heteroarenes and aliphatic C-H components has been achieved via a radical pathway. This cross-dehydrogenative coupling method features a broad scope of substrates. The green oxidant H2O2 is used as a hydrogen atom transfer reagent, which is environmentally benign, low cost, and atom economical.

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Properties and Exciting Facts About 5-Nitroquinoxaline

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A highly active catalyst for the reductive cyclization of ortho-nitrostyrenes under mild conditions

A mild and efficient method for the palladium-catalyzed reductive cyclization of ortho-nitrostyrenes to afford indoles is reported. Treatment of ortho-nitrostyrenes with 0.1 mol% palladium (II) trifluoroacetate [Pd(TFA) 2] and 0.7 mol% 3,4,7,8-tetramethyl-1,10-phenanthroline (tm-phen) in DMF at 15 psig CO and 80C afforded indoles in good to excellent yields. When the reaction was conducted in toluene, the corresponding N-hydroxyindole was isolated. A mechanism that accounts for the formation of N-hydroxyindole is proposed.

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Rhodium-Catalyzed NH-Indole-Directed C-H Carbonylation with Carbon Monoxide: Synthesis of 6H-Isoindolo[2,1-a]indol-6-ones

An efficient synthesis of 6H-isoindolo[2,1-a]indol-6-ones through rhodium-catalyzed NH-indole-directed C-H carbonylation of 2-arylindoles with carbon monoxide has been developed. Preliminary mechanistic studies revealed that this reaction proceeds via N-H bond cleavage and subsequent C-H bond cleavage. Reaction monitoring via ESI-MS was used to support the formation of five-membered rhodacycle species in the catalytic cycle.

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Top Picks: new discover of 2,3-Dichloroquinoxaline

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Pyrido[1′,2′:4,5][1,4]oxazino[2,3-b]quinoxalines and pyrrolo[1′,2′:4,5][1,4]oxazino[2,3-b]quinoxalines

This disclosure describes substituted 2,3,3a,4-tetrahydro-1H-pyrrolo[1′,2′:4,5][1,4]oxazino[2,3-b]quinoxalines and 1,2,3,4,4a,5-hexahydropyrido[1′,2′:4,5][1,4]oxazino[2,3-b]quinoxalines which possess anxioyltic activity.

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18671-97-1, Catalysts are substances that increase the reaction rate of a chemical reaction without being consumed in the process. 18671-97-1, Name is 2,6-Dichloroquinoxaline, molecular formula is C8H4Cl2N2. In a Article, authors is Mrsic, Natasa£¬once mentioned of 18671-97-1

Asymmetric hydrogenation of quinoxalines catalyzed by iridium/PipPhos

A catalyst made in situ from the (cyclooctadiene)iridium chloride dimer, [Ir(COD)Cl]2, and the monodentate phosphoramidite ligand (S)-PipPhos was used in the enantioselective hydrogenation of 2- and 2,6-substituted quinoxalines. In the presence of piperidine hydrochloride as additive full conversions and enantioselectivities of up to 96% are obtained.

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Quinoxaline – Wikipedia,
Quinoxaline | C8H6N1677 | ChemSpider

Extended knowledge of 2-Chloroquinoxaline

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1448-87-9, Name is 2-Chloroquinoxaline, belongs to quinoxaline compound, is a common compound. 1448-87-9In an article, authors is Baranova, Anna A., once mentioned the new application about 1448-87-9.

Synthesis and characterization of linear 1,4-diazine-triphenylamine?based selective chemosensors for recognition of nitroaromatic compounds and aliphatic amines

Novel 1,4-diazine-based dyes of the D?pi?A type, possessing triphenylamine as an electron-donating group, have been developed. Fluorescence studies have demonstrated that emission of these fluorophores is sensitive towards different nitroaromatic compounds and aliphatic amines, both in solutions and in a vapor phase. Moreover, these compounds can be considered as ?naked-eye? fluorescent probes for solution polarity because they possess pronounced solvatochromic properties. Therefore, these compounds have to be regarded as potential multifunctional chemosensors for monitoring hazardous organic substances.

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Synthesis of thieno[2,3-b]quinoxalines from 2-haloquinoxalines

Thieno[2,3-b]quinoxalines were synthesized from 2-haloquinoxalines using palladium catalyst. The coupling of latter with alkynes and addition of one mol equivalent of bromine to the 2-alkynylquinoxalines thus produced was described. The resulting dibromides reacted with dipotassium trithiocarbonate to produce the desired compound.

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